The Synthesis And Self-assembly Properties Of Two Types Of Hexazatriphenlene Systems

This thesis is focused on the synthesis and self-assembly properties of two typesof hexazatriphenlene derivatives. It consists of the following two parts:In the first part, an achiral discotic conjugated molecule HPHAT was synthesized.It could co-assemble with chiral amino acid derivatives to form1:3supramolecularcomplexes in CHCl3driven by intermolecular hydrogen-bonding, as revealed by NMRtitration, ESI-MS, and infrared spectroscopy experiments. The binding constants of thecomplexes could reach a magnitude of104M-1and they existed in solution as singlecomplexes, instead of high ordered aggregates, which was evidenced by UV-vis andNMR dilution experiments and DLS study. In the next step, this kind ofsupermolecules was investigated by circular dichroism spectroscopy. It was found theyhad chiral propeller-like structures. Both “sergeants–and-soldiers” principle and“majority-rule” effect have been found applicable in these discrete four-componentsupermolecules, which are the simplest supramolecular system ever reportedexhibiting chiral amplification. DFT calculations were further performed to understandthe mechanism of origination of the chiral structures.In the second part, we designed a series of conjugated compounds which containsthe hexazatriphenlene structure as kernel and the periphery was modified withdifferent number of thiophene units and long-chain alkyl groups. These compoundswere characterized by a series of techniques, including UV-vis, NMR, fluorescencespectroscopy, CV, DSC and SEM, which preliminarily revealed their optical,electrochemical and self-assembly properties.